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Our Favorite Words of Wisdom from Chicago Ideas Week 2018

On October 15 to 21, Chicago Ideas once again gathered more than 200 thought leaders and creators (and lots more audience members and guests) for a week full of high-energy programming. The eighth annual Chicago Ideas Week was full of memorable, hilarious, and beyond motivational conversations and interactive events that came with enough inspiration to last a lifetime (though, of course, the beauty of Chicago Ideas is that they’re always bringing us more). As journalist and New York Times bestselling author Cal Fussman said while hosting the “Life’s Big Questions” talk, “It’s just great that the whole city is given a week to celebrate big questions and big ideas.” It is indeed, and this year, we gathered plenty of food for thought throughout that process from some of the many incredible speakers.

On taking risks with your voice…“I do think it's good to be aware of when you've overstepped your bounds; but more in the sense that you are recognizing that there are boundaries, that there can be limitations, and sometimes it's okay to go over them—but you have to accept the consequences.”

On owning your uniqueness…“I feel like everyone thinks that they are funny. I think that your sense of humor is your sense of humor, and you laugh at what you think is funny, and you laugh at other people who you think are funny, therefore that is your sense of humor.”

On women making their voices heard…“My personal goal for myself, if I'm in a meeting, is I don’t leave the meeting without talking. [...] I'm very conscious of the fact that, once you are in the room, you [have to] use your voice. That's scary. Sometimes the opening's not there, [but] you [have to] create the opening and use your voice. [...] The other thing you can do when there's more than one of you in the room is support each other, so if there's more than one of you around the table—and men can do this too...you can support the women—make sure if not every voice has been heard around the table, say, ‘Can we hear what she [has to] say? Let's hear what Susan [has to] say, what Lily [has to] say, what Emma [has to] say.’ And if you're running the meeting...you have the power to make sure that everybody gets heard. [...] It's something everybody in this room can do: You can either support somebody in a meeting [or] call on somebody in a meeting.”

On going after your dream…“My advice is to do it—and to not believe the voices in your head that tell you that you can’t do it, to not believe the voices in your head that tell you there’s no time to do it or that you won’t be successful if you do it. That's a lie. Those voices are lies. I understand how busy you are, and you have a lot of kids, and you have a lot of responsibilities. Here are some things that you can do to create some time in your life: Delete all social media apps from your telephone. You have just freed up many hours. You'll be shocked how many hours you just freed up. [...] There are so many things you could do to create time if your passion project actually was your priority.”

On taking risks…“Risk is an interesting thing. [...] One of my great friends and mentors, Jon Krakauer (the author of Into Thin Air and Into The Wild) once said to me there's two great risks: risking too much and risking too little. We often look at risking too much, and we're always kind of on our heels a little bit like, ‘I'm afraid of that, I'm scared of that, I don't want to risk too much,’ but I think it's important when you’re asking yourself hard questions about what you do and your life to examine the idea of risking too little. That’s an important balance, to look at both sides of risk, because I personally don't want to risk too little.”

And on failure...“You have to try, and you have to fail, and you have to expect to fail. Failure can never be looked at as a permanent state. [...] Failures are your points of learning.”

On reframing setbacks...[After participating in a pageant that led to an entertainment career], "I didn't win. I came in third runner-up. [...But] even though I didn't win the pageant, what I did win was a career that I didn't even know [I would pursue]. Sometimes the Ls you take in life are stepping stones to the Ws. And so even though I didn't get the crown, I won.”

On helping others…“Everything that I have ever tried to do has had two motivations: One is I really do believe in trying to create social change; and then the other one is I'm scared and alone, too, so I would like for you to join me. I don't want to be the only one that's out here. And so...every job that I have, I try to make sure to hold the door open. That's my motto: If I get through, you’re coming with me; and I really believe in that wholeheartedly. And especially if I have more privilege than you, I’m holding the door for you even wider.”

On being yourself…“The idea of the authentic self is really the key. Everyone has an individuality that can’t be copied. The minute it’s copied, it’s false and it doesn’t look good. But if there’s an authentic beauty that is healthy and you’re the best version of yourself, that’s beauty that can’t be contested. It can’t be copied. [...] There’s nothing more beautiful; there’s nothing more stunning than authentic truth.”

On putting yourself out there…“The single most generous act we can do as humans is to create community. All we can do is reach out. It takes that step forward, it takes that, 'Okay I might be rejected'—but what does rejection even mean? It’s just trying.”

On finding bravery in darkness…“My mom...told me a lesson. She told me darkness is like a monster: If you let your fear win, then the darkness can devour you. So stare into the darkness, then the darkness will disappear. [...] I experienced a lot of darkness in my life...but I open my eyes as much as i can, and that is the way I learned how to fight against the darkness and be fearless.”

On believing in yourself…“Your gift, whatever [it] is for you, it's inside of you and you are not here…by a fluke. We trust everything: We trust that if we sit in this chair, the legs won't fail us. Trust yourself like you trust the chair you're sitting in, that you can do or be anything that you want to be.”

On harnessing fear and not letting it stop you… “Fear comes from the external expectations, and I really firmly believe that if you are in touch with yourself as an artist, that fear becomes an ally. It will never go away...you're always gonna bomb, but it will become something where you're like, ‘I'm used to it, and when it comes on I know it means I need to be working harder and putting myself out there more, staying ahead of it, staying in control.’ [...] Every time...you actually get out of your own way, and push the fear aside, and put it out into the world—whether it's a success or whether it's a failure—you do learn. It's undeniable. [...] I have no problem with failure and fear that comes from failure. I have a big problem with fear that makes people never jump off the diving board.”

On discovering Chicago as a transplant...“What delighted me is what a wonderful city Chicago is. [...] There’s something special about this city. [...] People love their city. There is something palpable about how strongly people feel about this and how civic-minded this community is. People in businesses feel that it is their obligation to make sure they give back to their community. There’s a deep sense of pride here, and that’s been really really gratifying.”